Drunken Holiday Cheating ([M]25, [F]23)

Note: Both parties involved know we fucked up. This is not an AITA post, we already know ESH. Despite being a huge mistake, it was still incredibly hot.

—

I recently moved a few states over to live with some friends. These friends are a heterosexuals couple. Let’s call the guy Dan and the gal Jess. Dan is a close friend of mine I’ve know since 2010. Jess started dating Jess in early 2016. In addition to Dan entering a fantastic relationship, Jess’s introduction into our lives also gave me a new close friend. After nearly a year of living with each other, the majority of which has been spent quarantining, the three of us have become inseparable. Dan and Jess are the closest to friends I’ve ever had and this is the least toxic living arrangements I’ve ever had.

Dan had to leave the town for a couple days last week. Jess and I were having fun the first few days just playing video games, binging shows, consuming edibles, and making gingerbread houses to celebrate the season. Two nights before Dan’s return, Jess and I were playing Mario Party while drinking and this somehow led to her asking about an ex of mine that I try to avoid discussing whenever possible. The alcohol had destroyed my inhibitions this night though and I talked very openly about that past relationship and somehow talking about this got to me discussing my sex life. This lead to talking about Jess and Dan’s sex life. And this led comparing and contrasting the different kinks and fetishes we’re interested in and have participated in. We discovered a mutual appreciate for exhibitionism and lamented how neither of us have ever really lived out such a fantasy. In our drunken stupor we convinced ourselves she wouldn’t be cheating on Dan if we were just watching each other masturbate, so long as never came into physical contact.

We went into the hallway, where if we went to opposite sides of the hallway we’d be the furthest we possibly could in the house. Slowly we striped, watching each other the whole time. Jess is a 5’6, has tits that are each about the size of a cantaloupe, puffy brown nipples, and has kept herself decently fit through quarantine. I think we were both fully intent on fucking tonight, but we had to make some excuses to get there. We made excuses about need to be closer to each other while we watched. Since we’d decided to no longer worry about not being close to each other, we moved to the living room and sat the couch across from each other. Then we justified sitting rightly next to each other, because we’d have done that platonically with our clothes on before. And after several minutes of allowing our naked bodies to sit next to each others, she rolls on top of me and says “As long as there’s no penetration we’re not doing anything wrong.”

We feel each other up and let our now bodies, now slick with sweat at this point, slide all over each other. I caressed her cheek and pulled her face closed to mine. “It’s not cheating if we don’t use tongue,” I said. We kissed with out mouths closed. As my dick slid across her thighs I knew my precum was already getting all over her body. Suddenly my dick and her flower found each other. My cock slid across her lips and over her clit. Our juices were mixing, but yet we hadn’t penetrated.

After our outercourse lasted for several minutes and I knew I was going to be able to last much longer. “Fuck I’m gonna cum Jess,” I announced.

Jess: “I want you to cum inside me.”

Me: “But that’d break our rules.”

Jess: “We’ve already crossed the line when we got naked earlier. I want you in me right now. We’ll worry about any drama later.” I didn’t reply. She grabbed my dick and lined it up with her hole. “Is that okay?”

“Yeah.”

She dropped her hips and I penetrated her. We kissed again, this time with tongue. I had been so pent up and stimulated leading up to this point that just entering Jess while kissing her sent me into a sensory overload, and I burst inside of her immediately. She continued to ride me while I was cumming, rubbing her own clit, and then she finished up. While we were both feeling the waves of pleasure from our orgasms she fell limp on top of me and sighed loudly. We continued to make out as we came down from our orgasmic highs.

After cuddling for a few minutes, the feelings of guilt started to set in. “Hey, uh, I’m gonna go take a shower,” I said. I needed to think things through and process what just happened, and I did feel a bit filthy from all of sex we got on us. I ran upstairs to my room and got a fresh towels and clothes and hopped in my shower.

As I shampooed my hair the shower curtain opened. “I gotta shower too.” She got into the shower and then held me close. “If Dan never knows… no one gets hurt.” She sounded genuinely sad and I knew we fucked up big time.

After we got cleaned up and dried off, we went to our separate bed rooms and turned in for the night. I started wacking off in bed, thinking about how hot this sexual interaction with Jess had been today, and my guilt about how this could hurt Dan started to morph into a perverse pleasure, knowing that Jess and I could have done anything and so long as Dan never knew, no one would get hurt.

I get a notification of my phone. It’s a Snapchat from Jess. It’s a picture of her laying in bed in only her bra and panties. “If we already crossed the line, we might as well sleep in the same bed.” I quickly roll out of bed and headed to their bedroom. I got under the covers in only my boxers. We cuddled close, letting our nearly naked bodies touch once again.

As I fell asleep I wondered about what we would decide to do about this after we woke up. Jess had cheated on Dan with me, and Dan is my best friend. This could ruin everything for us. But I forced myself to fall sleep knowing that Dan wouldn’t be home under the day after next. We had more than enough time to figure out what to do, and whether we wanted to do more.

What happened on the next day… well that’s another story in itself.

Source: reddit.com/r/gonewildstories/comments/kl0ph7/drunken_holiday_cheating_m25_f23